Winsted, CT Homes

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  $329,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  107 Peck Rd, Winsted, CT 06098

  Turnkey 3 Bedroom, 1 bathroom home on almost an acre in Winchester. The home is sited up a long driveway in a quiet, wooded setting across from state land. Completely renovated by current owner, top to bottom. Updated kitchen & bath, new roof, new hot water heater, new Trex deck, new pellet stove, new ductless mini splits in living area and primary bedroom and much more! Attached one car garage

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  (860) 855-0150

  107 Peck Rd, Winsted, CT 06098
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  /20

  $2,300 total monthly price

  • 3 Beds
  • 1.5 Baths
  • 1,654 Sq Ft
  • House for Rent

  220 Walnut St, Winsted, CT 06098

  Location, location, location! Just a short drive to the shores of the ever-popular Highland Lake, you must put 220 Walnut St. at the top of your list. Lovingly updated (while keeping all of its antique charms) and customized by a local artist. This offering, ready for immediate occupancy, is a true must-see in person. The heating system has been replaced, new appliances, newer roof, fresh paint,

  Justin Mokerzecki Glanville Real Estate

  220 Walnut St, Winsted, CT 06098
• 

  $269,000 Sold May 05, 2025

  39 Finn St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,175 Sq Ft
  • Built 1880

  Last Sold Summary

  • $229/SF
  • 35 Days On Market

  Current Estimated Value $264,910

  Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  39 Finn St, Winsted, CT 06098
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  Est $238,522 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  174 Wallens St Unit D2, Winsted, CT 06098

  174 Wallens St Unit D2, Winsted, CT 06098
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  /2

  $49,000

  • Land
  • 0.37 Acre
  • $132,432 per Acre

  99 Hubbard St, Winsted, CT 06098

  99 Hubbard St. - Private Lot Near Downtown & Highland Lake. Tucked away at the end of a quiet dead-end street, this .37-acre lot offers both privacy and convenience. While enjoying a peaceful setting, you're still just minutes from downtown with easy access to shopping, dining, and entertainment. Plus, Highland Lake is just a short distance away, providing endless opportunities for boating,

  

  David Sartirana

  Northwest CT Realty

  (860) 946-4468

  99 Hubbard St, Winsted, CT 06098
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  /11

  $2,200 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Townhouse for Rent

  188 E Lake St, Winsted, CT 06098

  Welcome to our beautiful lakeside apartment! 2 bedroom/1 Bath. Situated on the picturesque shores of Highland Lake, this fully renovated and furnished apartment offers stunning views and serenity. The apartment features a spacious living area, a fully equipped kitchen, huge primary bedroom with lake views, dedicated office space and in unit laundry. Whether you are looking for a peaceful retreat

  Annie Simard LPT Realty

  188 E Lake St, Winsted, CT 06098
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  $227,500 Sold Nov 20, 2025

  174 Wallens St Unit H1, Winsted, CT 06098

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft
  • Built 2007

  Last Sold Summary

  • 3% Below List Price
  • $171/SF
  • 91 Days On Market

  Last Listing Agent Kim D'Andrea William Pitt Sotheby's Int'l

  174 Wallens St Unit H1, Winsted, CT 06098
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  Est $240,771 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft

  174 Wallens St Unit D1, Winsted, CT 06098

  174 Wallens St Unit D1, Winsted, CT 06098
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  /37

  $499,999

  • 5 Beds
  • 4 Baths
  • 5,016 Sq Ft

  55 Walnut St, Winsted, CT 06098

  Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family

  

  David Sartirana

  Northwest CT Realty

  (860) 390-5071

  55 Walnut St, Winsted, CT 06098
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  $190,000 Sold May 15, 2025

  154 Wallens St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1905

  Last Sold Summary

  • 13% Below List Price
  • $103/SF
  • 20 Days On Market

  Current Estimated Value $196,724

  Last Listing Agent Adam Devine Dorrance Realty

  154 Wallens St, Winsted, CT 06098
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  Est $284,322 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,946 Sq Ft

  174 Wallens St Unit C3, Winsted, CT 06098

  174 Wallens St Unit C3, Winsted, CT 06098
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  /38

  $1,270,000

  • 3 Beds
  • 3 Baths
  • 2,420 Sq Ft

  722 Lake Dr, Winsted, CT 06098

  Welcome to lake living at its finest! Built in 2014 and first time on the market. Impeccably maintained, this stunning three bedroom, 3 bath home on Highland Lake, Winchester offers the perfect blend of comfort, style, and breathtaking VIEWS! From the moment you enter you will be captivated by the open-concept design, high-end finishes and panoramic lake views from both inside and out. Enjoy

  Joanne Donne The Washington Agency

  722 Lake Dr, Winsted, CT 06098
• 

  $277,000 Sold Oct 09, 2025

  12 Cherry St, Winsted, CT 06098

  • 4 Beds
  • 1 Bath
  • 1,492 Sq Ft
  • Built 1800

  Last Sold Summary

  • 4% Below List Price
  • $186/SF
  • 54 Days On Market

  Last Listing Agent Susan MCGHEE The Washington Agency

  12 Cherry St, Winsted, CT 06098
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  Est $285,029 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  17 Colony Dr, Winsted, CT 06098

  17 Colony Dr, Winsted, CT 06098
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  $749,999 Under Contract

  • 5 Beds
  • 2.5 Baths
  • 2,950 Sq Ft

  151 Losaw Rd, Winsted, CT 06098

  This property is your personal sanctuary, complete with private trails for hiking your own land. Feel worlds away while being less than 2 miles to town amenities in this like-new retreat nestled on an expansive 11.59-acre lot. The eat-in-kitchen is well-equipped with ample cooking space, seamlessly connected to the formal dining room and open to living space, and leads out to the large deck with

  Breanna Goebel Compass Connecticut, LLC

  151 Losaw Rd, Winsted, CT 06098
• 

  $160,000 Sold Apr 29, 2025

  14 Riveredge Dr Unit 14, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 992 Sq Ft
  • Built 1986

  Last Sold Summary

  • $161/SF
  • 0 Days On Market

  Current Estimated Value $163,920

  Last Listing Agent Maria Smith KW Legacy Partners

  14 Riveredge Dr Unit 14, Winsted, CT 06098
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  Est $285,729 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  159 Pratt St, Winsted, CT 06098

  159 Pratt St, Winsted, CT 06098
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  /40

  $299,900 Pending

  • 4 Beds
  • 3 Baths
  • 1,874 Sq Ft

  106 Rockwell St, Winsted, CT 06098

  Looking to expand your investment portfolio-or live nearly rent-free while building one? This rare 3-family opportunity checks all the boxes! Hard to come by, this multi-family property features long-term, reliable tenants plus a vacant unit ready for an owner-occupant or a new rental. The lower level offers a comfortable 1-bedroom unit with walk-out patio. The main (2nd) level features 2

  Dawn Rousseau Showcase Realty, Inc.

  106 Rockwell St, Winsted, CT 06098
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  $225,000 Sold Jul 03, 2025

  39 Baker St, Winsted, CT 06098

  • 5 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Built 1900

  Last Sold Summary

  • $140/SF
  • 166 Days On Market

  Current Estimated Value $231,787

  Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  39 Baker St, Winsted, CT 06098
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  Est $219,513 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  17 Front St, Winsted, CT 06098

  17 Front St, Winsted, CT 06098
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  /40

  $419,000

  • 4 Beds
  • 1.5 Baths
  • 2,365 Sq Ft

  187 Torringford St, Winsted, CT 06098

  Welcome to 187 Torringford Rd! Set on a beautiful 4-acre lot, this spacious 4-bedroom home offers the perfect blend of natural light, character, and country living. Step inside through the mudroom, also serving as a convenient laundry area, and head up to a charming loft that overlooks the bright, window filled kitchen. The kitchen features an abundance of natural light and provides a warm,

  Jessica Washington William Raveis Real Estate

  187 Torringford St, Winsted, CT 06098
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  $45,000 Sold May 09, 2025

  269 Walnut St, Winsted, CT 06098

  • Land
  • 0.5 Acre
  • $90,000 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 72 Days On Market

  Current Estimated Value $157,000

  Last Listing Agent David Sartirana Northwest CT Realty

  269 Walnut St, Winsted, CT 06098
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  Est $441,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,969 Sq Ft

  319 Taylor Brook Rd, Winsted, CT 06098

  319 Taylor Brook Rd, Winsted, CT 06098
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  /17

  $319,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,754 Sq Ft

  25 Center St, Winsted, CT 06098

  Don't miss this unique opportunity to own a multi family residential property and an office space! (Owner currently has permission from the town to create a 2nd residential unit on the first floor) - will have 2.5 baths when completed. Great central location close to all amenities that Winsted has to offer including restaurants, parks, college, public transportation and shopping. First floor

  Tony Goia The Washington Agency

  25 Center St, Winsted, CT 06098
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  $1,575,000 Sold Jun 30, 2025

  508 W Wakefield Blvd, Winsted, CT 06098

  • 7 Beds
  • 4 Baths
  • 2,687 Sq Ft
  • Built 1890

  Last Sold Summary

  • 5% Below List Price
  • $586/SF
  • 316 Days On Market

  Current Estimated Value $1,583,006

  Last Listing Agent Pierre Moran William Pitt Sotheby's Int'l

  508 W Wakefield Blvd, Winsted, CT 06098
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  Est $265,327 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  39 Rockwell St, Winsted, CT 06098

  39 Rockwell St, Winsted, CT 06098
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  $389,000

  • Land
  • 20.87 Acres
  • $18,639 per Acre

  7 Stadler Heights, Winsted, CT 06098

  Welcome, You be the first, to come and conquer this land here in Winchester, Connecticut. There are 20.87 acres of virgin land. Come and build, do what you do best, you can have Peace and Privacy!!! There are no sidewalks, no streets that drive through. You are 40 minutes from multiple private schools. 16 minutes from Charlotte Hungerford Hospital. 1 hour from Tweed Airport New Haven. 39

  Hector Ortiz KW Legacy Partners

  7 Stadler Heights, Winsted, CT 06098
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  $400,000 Sold Mar 03, 2025

  296 Colebrook Rd, Winsted, CT 06098

  • 7 Beds
  • 3.5 Baths
  • 4,253 Sq Ft
  • Built 1958

  Last Sold Summary

  • 24% Below List Price
  • $94/SF
  • 132 Days On Market

  Last Listing Agent David D'Amore Northwest CT Realty

  296 Colebrook Rd, Winsted, CT 06098
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  Est $275,564 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,114 Sq Ft

  160 Glendale Ave, Winsted, CT 06098

  160 Glendale Ave, Winsted, CT 06098
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  $849,900

  • 4 Beds
  • 2 Baths
  • 1,781 Sq Ft

  119 W Wakefield Blvd, Winsted, CT 06098

  Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

  Mela Veltri Case KW Legacy Partners

  119 W Wakefield Blvd, Winsted, CT 06098
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  $279,900 Sold Sep 12, 2025

  39 Colony Dr, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,183 Sq Ft
  • Built 1969

  Last Sold Summary

  • $237/SF
  • 65 Days On Market

  Current Estimated Value $282,780

  Last Listing Agent Alison Behlman Tier 1 Real Estate

  39 Colony Dr, Winsted, CT 06098
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  Est $314,280 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,544 Sq Ft

  153 Mathew Rd, Winsted, CT 06098

  153 Mathew Rd, Winsted, CT 06098
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  /34

  $749,900

  • 7 Beds
  • 3 Baths
  • 3,486 Sq Ft

  39 S Main St, Winsted, CT 06098

  THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas

  RYAN HORVAY Smith & DeGroat Real Estate

  39 S Main St, Winsted, CT 06098
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  $279,000 Sold May 19, 2025

  56 Lakeview Rd, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,101 Sq Ft
  • Built 1956

  Last Sold Summary

  • 16% Above List Price
  • $253/SF
  • 6 Days On Market

  Current Estimated Value $244,272

  Last Listing Agent Tony Goia The Washington Agency

  56 Lakeview Rd, Winsted, CT 06098
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  Est $208,996 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,626 Sq Ft

  111 Torringford St Unit 19, Winsted, CT 06098

  111 Torringford St Unit 19, Winsted, CT 06098
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  /40

  $2,199,000

  • 9 Beds
  • 5.5 Baths
  • 7,000 Sq Ft

  431 W Wakefield Blvd, Winsted, CT 06098

  LOCAL NEWS JUST ANNOUNCED THAT WINSTED WAS 1 OF THE MOST DESIRABLE TOWNS TO LIVE WITH EMPHASIS ON BEAUTIFUL HIGHLAND LAKE. This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into

  Lisa Ogren Berkshire Hathaway NE Prop.

  431 W Wakefield Blvd, Winsted, CT 06098
• 

  $679,000 Sold Apr 30, 2025

  110 South Rd, Winsted, CT 06098

  • 4 Beds
  • 3 Baths
  • 3,870 Sq Ft
  • Built 1984

  Last Sold Summary

  • $175/SF
  • 5 Days On Market

  Current Estimated Value $697,142

  Last Listing Agent Matthew Egan Regency Real Estate, LLC

  110 South Rd, Winsted, CT 06098
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  Est $214,978 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,204 Sq Ft

  111 Riverton Rd Unit 30, Winsted, CT 06098

  111 Riverton Rd Unit 30, Winsted, CT 06098
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  $395,000

  • 3 Beds
  • 1.5 Baths
  • 1,909 Sq Ft

  720 Main St, Winsted, CT 06098

  Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building located on bustling Main Street, most recently home to "JT's Cafe," and previously known as "The Winning Ticket Cafe." The first-floor commercial space includes features such as an existing kitchen area with oven range vents, fridge, bathroom, and open seating area. Great potential for a new restaurant, cafe,

  Ryan Marconi The Washington Agency

  720 Main St, Winsted, CT 06098
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  $326,000 Sold Oct 31, 2025

  62 Fruit St Unit 64, Winsted, CT 06098

  • 6 Beds
  • 2 Baths
  • 3,078 Sq Ft
  • Built 1902

  Last Sold Summary

  • $106/SF
  • 13 Days On Market

  Last Listing Agent Antonio De La Cruz Eagle Eye Realty PLLC

  62 Fruit St Unit 64, Winsted, CT 06098

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